Earlier boats were completed as Oyster 53s before the model evolved into the 55. By the builder’s own admission, the change involved little more than “fiddling with the transom” of its predecessor. Built on a semi-custom basis from 1986 onward, just under fifty examples have been completed. Original owners chose their interiors, wood finishes, and decor. Most opted for teak, though boats finished in light oak, cherry, and ash also left the mold.
Design and Construction
The Oyster 55 measures 56 feet 3 inches overall, with a 45-foot-6-inch waterline and a 15-foot-9-inch beam. It displaces 51,000 pounds and has a canoe underbody, modified fin keel, and skeg-hung rudder. Buyers seeking different grounding characteristics could specify an optional high-performance bulb or Scheel keel.
The hull earned an average construction score of 10 in reader surveys. Bulkheads, the hull/deck joint, and chainplates all received perfect 10s. The balsa-cored deck scored 9, stringers and floors averaged 8, and exterior stainless earned a more modest 7.
A well-insulated engine compartment sits beneath the center cockpit and is spacious enough to accommodate a generator. The deck saloon arrangement gives the boat its long-waterline, volume-rich profile.
Rig, Machinery, and Handling
Every Oyster 55 is a saloon-deck cutter. Almost all carry furling headsails and staysails, along with in-mast furling mainsails. A typical setup combines a Hood Stoway spar with Hood headsail-furling systems for both the yankee and staysail.
Only three boats were built as ketches; the rest are sloops. The tall rig drives a large sail area of 1,672 square feet with a 150 percent headsail. The Displacement/Length ratio is 242, and the Sail Area/Displacement ratio is 19.5.
Under power, a typical installation is an 82-horsepower Perkins driving a three-bladed feathering Max Prop. Steering is through a Whitlock Premier pedestal.
Reader surveys gave the Oyster 55 a 9 for motion in a seaway. Deck safety, the reefing setup, and watertightness below decks also scored 9. Light-air and upwind performance received only 7s, but the boat scored between 9 and 10 in conditions ranging from a moderate breeze to storms. Downwind running earned a 9.
Accommodations
Andrew Winch designed the raised saloon around a curved settee to starboard and a loveseat to port. A teak-and-holly sole complements the teak joinery, which survey respondents rated a perfect 10 for cabinetry. The saloon table also received a perfect 10.
True upper and lower sea berths sit to starboard, just forward of the dinette, and to port, just aft of the companionway. The aft cabin has a double berth, and two heads serve the accommodation plan.
The navigation station lies to port of the companionway and scored between 9 and 10. The galley includes a four-burner gas range, refrigerator/freezer, and double sinks. Readers rated it an average 8 as a seagoing tool, with 8.5 for storage and 9 for overall efficiency.
The below-deck liveaboard plan earned an uncompromising 10. Sea-berth quality was less highly rated, averaging 7 to 8, while wet-gear stowage scored 7.
Performance and Rally Record
The Oyster 55 has a competitive streak. Its successes include twice topping the points table at Antigua Race Week, where Flying Scotsman won the overall cruising division twice. The design has also recorded ARC class wins and successes in the Europa Rally.
It is the single most prolific boat choice for the Trade Winds Round the World Rally, with seven examples having taken part. That record is a testament to the short-handed bluewater remit Holman & Pyle were given.
Ownership, Equipment, and Refits
Because each hull was semi-custom, owners individually specified the wood species, equipment level, and either a three- or four-cabin layout. Many boats have electric drive and electric primary winches. Almost all are fitted with Perkins 4236 84-horsepower diesels and Westerbeke generators.
Practical cruising provisions include a self-draining life-raft locker in the aft deck and a capacious lazarette. Readers gave the Oyster 55 an overall offshore rating of 9.5. Cockpit protection scored between 8 and 9, while dryness on deck received an 8.
Verdict
The Oyster 55 is a heavily built, thoughtfully arranged bluewater cutter. Its semi-custom origins allowed each owner to tailor the interior without compromising a structurally impeccable hull. Manageable furling rigs suit a short-handed crew, and the boat performs strongly in moderate to heavy air. Its light-air and upwind scores, however, show the limits imposed by its displacement.
Pros
- Impeccable hull, bulkhead, and chainplate construction in owner surveys
- Deck-saloon volume and a liveaboard plan that readers rated a perfect 10
- Proven short-handed rally and racing record, including the Trade Winds Round the World Rally
- Semi-custom interiors with owner-selected wood and three- or four-cabin layouts
Cons
- Light-air and upwind performance scored only 7 in reader surveys
- Sea-berth quality and wet-gear stowage received relatively low scores of 7 to 8
- Exterior stainless averaged 7, a weak point beside the otherwise flawless structural scores
